93296-10-7

Upstream product

• 586-77-6 4-bromo-N,N-dimethylaniline 
• 7646-85-7 zinc(II) chloride 
• 13190-50-6 4-dimethylaminophenyllithium 
• 7353-91-5 4-dimethylaminophenylmagnesium bromide 
• 108949-55-9 4-N,N-dimethylaminophenyl magnesium chloride 

Downstream Products

• 130447-14-2 4'''-Dimethylamino-[1,4';1',1'';4'',1''']quaterphenyl-4-carbonitrile 
• 2143-87-5 N,N-dimethyl-4-(4-nitrophenyl)aniline 
• 1171049-69-6 [(C₅(CH₃)5)ZrCl₂(CH₃C₉H₅C₆H₄N(CH₃)2)] 
• 18158-44-6 4-dimethylamino-4'-methoxybiphenyl 
• 1395463-53-2 4'-benzyl-N,N-dimethyl-[1,1'-biphenyl]-4-amine 
• 359653-43-3 2-(4-N,N-dimethylaminophenyl)naphthalene 
• 62056-42-2 (E)-3-[(4-N,N-dimethylaminophenyl)]-1-phenylpropene 

Relevant academic research and scientific papers

The Formation of P-C Bonds Utilizing Organozinc Reagents for the Synthesis of Aryl- A nd Heteroaryl-Dichlorophosphines

Aryl- A nd heteroaryl-dichlorophosphines are mildly and selectively made in a one-pot synthesis in moderate to good yields starting from the respective aryl bromides or five-membered heterocycles, following lithiation with nBuLi, transmetalation with ZnCl

Palladium-catalyzed secondary benzylic imidoylative reactions

Reported herein is a palladium-catalyzed secondary benzylic imidoylative Negishi reaction leveraging the sterically bulky aromatic isocyanides as the imine source. This method allows the facile access of alkyl-, (hetero)aryl-, and alkynylzinc reagents to afford various α-substituted phenylacetone products under mild acidic hydrolysis, which are ubiquitous motifs in many pharmaceuticals and biologically active compounds. The diastereoselective reduction of imine can be accomplished to provide the expedient conversion of secondary benzylic halide into α-substituted phenethylamine derivatives with high atom economy.

Copper-Catalyzed Electrophilic Thiolation of Organozinc Halides by Using N-Thiophthalimides Leading to Polyfunctional Thioethers

(Hetero)aryl, benzylic, and alkyl zinc halides were thiolated with N-thiophthalimides at 25 °C within 1 h in the presence of 5–10 % Cu(OAc)2?H2O to furnish the corresponding polyfunctionalized thioethers in good yields. This electrop

Rhodium-Catalyzed Arylzincation of Alkynes: Ligand Control of 1,4-Migration Selectivity

The addition of arylzinc reagents ArZnCl 1 to alkynes 2 was found to be catalyzed by rhodium complexes in the presence of a catalytic amount of zinc chloride. The selectivity in giving 2-arylalkenylzinc species 3 or ortho-alkenylarylzinc species 4, the la

Nickel-catalyzed cross-coupling of β-carbonyl alkenyl pivalates with arylzinc chlorides

The nickel-catalyzed cross-coupling reaction of β-carbonyl alkenyl pivalates with arylzinc reagents generates 3-aryl-substituted α,β-unsaturated carbonyl compounds via C-O bond cleavage. The reaction features mild reaction conditions, a wide scope of substrates, and good functional group tolerance.

Directed Zincation or Magnesiation of the 2-Pyridone and 2,7-Naphthyridone Scaffold Using TMP Bases

A regioselective zincation of the 2-pyridone and 2,7-naphthyridone scaffolds has been developed. Zincations of the methoxyethoxymethyl (MEM)-protected compounds using TMP2Zn·2MgCl2·2LiCl (TMP = 2,2,6,6-tetramethylpiperidyl) followed

Transition-Metal-Free Cross-Coupling of Aryl and Heteroaryl Thiols with Arylzinc Reagents

Cross-coupling of (hetero)arylthiols with arylzinc reagents via C-S cleavage was performed under transition-metal-free conditions. The reaction displays a wide scope of substrates and high functional-group tolerance. Electron-rich and -deficient (hetero)arylthiols and arylzinc reagents can be employed in this transformation. Mg2+ and Li+ ions were demonstrated to facilitate the reaction.

Preparation of Polyfunctional Naphthyridines by Cobalt-Catalyzed Cross-Couplings of Halogenated Naphthyridines with Magnesium and Zinc Organometallics

CoCl2 (5%) catalyzes cross-couplings of various halogenated naphthyridines with alkyl- and arylmagnesium halides. Also, arylzinc halides undergo smooth cross-couplings with various naphthyridines in the presence of CoCl2·2LiCl (5%) a

Mild Cobalt-Catalyzed Negishi Cross-Couplings of (Hetero)arylzinc Reagents with (Hetero)aryl Halides

A catalytic system consisting of CoCl2?2 LiCl (5 mol %) and HCO2Na (50 mol %) enables the cross-coupling of various N-heterocyclic chlorides and bromides as well as aromatic halogenated ketones with various electron-rich and -poor ar

Efficient Synthesis of Diaryl Ketones by Nickel-Catalyzed Negishi Cross-Coupling of Amides by Carbon–Nitrogen Bond Cleavage at Room Temperature Accelerated by a Solvent Effect

The first Negishi cross-coupling of amides for the synthesis of versatile diaryl ketones by selective C?N bond activation under exceedingly mild conditions is reported. The cross-coupling was accomplished with bench-stable, inexpensive precatalyst [Ni(PPh3)2Cl2] that shows high functional-group tolerance and enables the synthesis of highly functionalized diaryl ketone motifs. The coupling occurred with excellent chemoselectivity favoring the ketone (cf. biaryl) products. Notably, this process represents the mildest conditions for amide N?C bond activation accomplished to date (room temperature, 10 min). Considering the versatile role of polyfunctional biaryl ketone linchpins in modern organic synthesis, availability, and excellent functional-group tolerance of organozinc reagents, this strategy provides a new platform for amide N?C bond/organozinc cross-coupling under mild conditions.